1,3-Propanediol → 5-Bromo-2-(1,3-dioxan-2-yl)pyridine

HRID 1400896Notes

Reaction equation

HRID 1400896 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]=[O:9])=[N:6][CH:7]=1.[CH2:10](O)[CH2:11][CH2:12][OH:13]>C1(C)C=CC=CC=1.CC1(C)C2(CS(O)(=O)=O)C(CC1CC2)=O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]2[O:13][CH2:12][CH2:11][CH2:10][O:9]2)=[N:6][CH:7]=1

Participants

5

Reactant 2

HCID 104421,3-PropanediolHCID 98775625-Bromopyridine-2-carbaldehyde

Product 1

HCID 584745645-Bromo-2-(1,3-dioxan-2-yl)pyridineYield 101.9%

Reagents, catalysts & solvents 2

HCID 18462Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-CatalystHCID 1140TolueneSolvent

Procedure

To solution of 5-bromo-2-formylpyridine (10 g, 53.8 mmol), 1,3-propanediol (3.89 mL, 53.8 mmol) in toluene (30 mL) was added CSA (1.249 g, 5.38 mmol). The reaction mixture was heated to reflux for 4 h with a Dean-Stark trap. The reaction mixture was quenched by addition of saturated solution of sodium bicarbonate and extracted with EtOAc. The organic layer was washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated to afford compound 278 (13.37 g, 54.8 mmol, 101% yield, crude) as a brown solid that was used in the next step with no additional purification. MS (m/z): 244.06-246.06 (M+H).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 4 h with a Dean-Stark trap
  3. customThe reaction mixture was quenched by addition of saturated solution of sodium bicarbonate
  4. extractionextracted with EtOAc
  5. washThe organic layer was washed with brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-4a989d3c1f1a40e0895152be40301662
Source dataset
uspto-grants-2014_12
Patent number
US08906852B2

Reaction notes

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